Article

Journal of Chemical Crystallography

, Volume 35, Issue 9, pp 723-729

Hydrogen bonding in aromatic formamides

  • Matthias ZellerAffiliated withDepartment of Chemistry, Youngstown State University
  • , Robert J. WilcoxAffiliated withDepartment of Chemistry, Youngstown State University
  • , Floyd G. SnyderIIIAffiliated withDepartment of Chemistry, Youngstown State University
  • , Harry A. SeibelIIAffiliated withDepartment of Chemistry, Youngstown State University
  • , Nathan J. TakasAffiliated withDepartment of Chemistry, Youngstown State University
  • , Allen D. HunterAffiliated withDepartment of Chemistry, Youngstown State University Email author 

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The solid state structures of two p-substituted aromatic formamides have been determined. p-Nitro formamido benzene (1) crystallizes in the monoclinic space group C2/c with a = 10.9859(7), b = 10.0576(7), c = 13.0331(9) Å, β = 97.148(1) and Z = 8. p-formamido anisole (2) crystallizes in the orthorhombic space group Pna21 with a = 10.5598(7), b = 7.6553(5), c = 9.2522(6) Å and Z = 4. Both compounds show hydrogen bonding in the solid state, forming infinite chains via N–H⋅ < eqid1 > ⋅O = C bridges. For the anisole formamide (2), the molecules exhibit in a zig-zag arrangement. The nitro compound (1) exhibits a spiral-like wavy line with a fourfold repeating unit, making it the first formamide having a chiral N–H⋅ < eqid2 > ⋅O bridged chain reminiscent of those found for α-helices in proteins. While the individual spirals of 1 are orientated either clockwise or counterclockwise, their orientation towards each other is random.

Key words

Formamides hydrogen bonding disorder infinite chain spiral disorder